Eyes Wide Open
by SophiaSalvatore2
Summary: Can Damon and Elena, best friends since childhood, risk everything for a possible future together, or will they lose each other with their eyes wide open? Is this the end of their story..everything they had, everything they did, buried in dust? AH/AU
1. She Will Be Loved

_**Eyes Wide Open: Can Damon and Elena, best friends since childhood, open their eyes to a possible future together, or will they lose each other with their eyes wide open? Is this the end of their story..everything they had, everything they did, buried in dust?**_

**A/N: Hi everyone! This is my first attempt at writing a multi-chapter story, so please be easy on me :) This story is like my baby and I have big plans for the story. It's going to be a rollercoaster so buckle-up and enjoy the ride! I'm about to be finished with school so I should be able to update as soon as I have time/inspiration. I already have the next chapter pretty much complete. I plan to update once I complete the chapter in advance..hopefully that will work out in the long run. Like I said, this is my first attempt at this, so please forgive me for any spelling/grammatical errors. Also, if you are interested in being a beta for me, I would definitely appreciate it! Anyways, enough of my ramblings...enjoy the first chapter "She Will Be Loved" of Eyes Wide Open.**

_Beauty queen of only eighteen_

_She had some trouble with herself_

_He was always there to help her_

_She always belonged to someone else_

_I drove for miles and miles_

_And wound up at your door_

_I've had you so many times but somehow_

_I want more_

_I don't mind spending everyday_

_Out on your corner in the pouring rain_

_Look for the girl with the broken smile_

_Ask her if she wants to stay a while_

_And she will be loved._

_**She Will Be Loved-Maroon 5**  
_

She withdrew her keys from her designer bag and slipped the key into the lock. As she stepped through the dark penthouse apartment, she felt her tiredness hit her in an instant rush. All she wanted to do was take off her pumps, her skin tight outfit, and get in a warm bed. Even through the darkness she followed the familiar path to the bedroom in the back. As she stepped further into the room she slipped off her shoes and pulled her shirt over her head. Finding his navy shirt on the floor next to the bed, she slipped it on her and removed her skirt. Using her hands to find her side of the bed, she sunk into the soft mattress and rolled to the familiar body next to her.

Feeling the new warmth next to him he moved closer and moved his arm over her thin waist and pulled the body right up against him. Tucking his head to the top of her head, he inhaled her scent and instantly relaxed further against her body.

The New York summer sun streamed through the window of the penthouse apartment. The light gleamed across the young woman's olive skin. The new warmth caused her to stir against the plush pillow. As she moved slightly from her comfortable sleep, she felt the weight of a familiar arm draped across her sheet covered waist. Gaining the energy to turn over, she rolled over to face the sleeping body of her best friend. Her gaze carried from his messy raven black hair, all the way down his muscular naked chest to the expensive black sheet that hung low on his waist.

_Why must he sleep with nothing but his boxers on? Oh I know, because he's Damon-freaking-Salvatore, that's why._

As she brought her brown doe eyes back to his chiseled face, she was surprised to see icy blue orbs staring back at her.

"No need to stare, it's real" his normally velvety voice came out in a sleep-induced raspy tone. With an eye roll, Elena pushed against his hard chest in annoyance, in hope to push the cockiness right out of him. But of course, her attempt turned out into a slight nudge that barely moved him. He took the opportunity to pull her closer and roll her underneath him. With his roaming hands he began to tickle her sides, right where he knew she was the most ticklish. Elena squirmed from underneath him, wheezing for a breath of air in between screaming for him to stop and laughing uncontrollably.

This is how it has always been between these two best friends. They have been friends since they came out of the womb. Elena's parents and Damon's parents happened to be friends ever since their college days at NYU. The continued their friendship after college and remained close friends throughout their entire lives. Their friendships were so ironically in sync that the Gilbert's and Salvatore's got pregnant around the same time. Miranda and Arianna shared their pregnancy joys together and even joked about planning their children's future wedding to each other. Aside from their jokes, they knew that their children would have a close bond and counted down the days to the arrival of their bundles of joy.

Coincidentally, Arianna and Miranda went into labor the same day. Twelve hours into labor Arianna gave birth to healthy twin boys, Damon the oldest by 10 minutes, and Stefan. Four hours after Miranda pushed out a beautiful baby girl named Elena.

The two families liked to joke about which Salvatore brother Elena would choose to marry. However, the three children became close friends instantly and quickly became inseparable. Then the Gilbert's added another child into their family, Jeremy. Elena and Jeremy were always close, but nothing compared to the relationship between Damon and Elena. There was something unexplainable about Damon and Elena. From a young age they formed an unbreakable bond that even Elena and Stefan didn't have. Damon and Elena understood each other with just a look, it's almost as if they had their own silent language between each other. They were very loyal and fiercly protective over one another. Even after 27 years of living and growing up together, their bond remained strong as ever.

"Damon...stop...please...I can't...breathe" she wheezed out. But instead of stopping, he continued on with torturing her. "Just admit it Elena" her name rolled off his tongue "you were staring, it's okay, I get it all the time." Through her fits of giggles she reluctantly gave in. "Fine Damon, I was staring." He finally stopped tickling but remained on top of her. "But it's nothing I haven't seen before. I mean our Mom's made us take baths together when we were younger."

"Oh but Elena, I've grown bigger since then" he stated while wiggling his eyebrows seductively.

"Alright Mr. Salvatore, that's enough" she pushed his chest and he fell on the mattress with a thud next to her body. With that, she pushed herself up on the bed and leaned against the headboard. She began to roll her neck side to side in hope to relieve some of the tension built up. Taking that as his queue, Damon slid behind her and started to massage her neck in all the right places. Not being able to control herself, Elena let out a moan.

"Another late night at the bar I'm guessing?" Elena's job as a bartender meant working into the wee hours of the night and dealing with countless inebriated idiots that decided to make her job a living hell. "You don't even want to know. I'm just so glad you live so close and I'm able to just crash here." The bar Elena worked at happened to be located right around the corner from Damon's penthouse. It was a lot more practical for her to just go to Damon's after her shift instead of trekking all the way to the other side of the city in the middle of the night. Which is why she often found herself waking up in her best friend's bed.

Their sleepovers weren't quite uncommon. Ever since they were little, they found themselves sleeping in each other's embrace. It was like their closeness protected them from everything and anything. They comforted each other and all it took was to be near each other.

He whispered into the hollow of her ear, "Well I know just the cure to your symptoms." Her eyes grew wide as she caught on to his ideas. She glanced over her shoulder and asked"Are you thinking what I'm thinking?"

"Chocolate chip waffles?"

"Hell yes!

* * *

"Ugh, I don't think I can move."

"Well maybe you should of thought about that before you inhaled those waffles"

"Oh c'mon Damon, you know these are the way to my heart. I can't just have one."

"Yeah you remind me of that every Sunday morning."

"So what are your plans for the rest of the day?"

"Well, I actually have a lunch date with this one chick that Stefan wants to set me up with. So I'll probably go meet up with Alaric after this and let him vent about his pathetic life. How about you sweet cheeks?"

"Funny you ask. I was actually wondering if I could shower at your place and then you might possibly be able to drop me off at Mason's apartment. I haven't seen him in a couple days and I thought I could spend the rest of the day with him."

Mason Lockwood, tall, dark, and handsome boyfriend of little miss Elena for the past 6 months. The couple met at the local coffee shop one morning, which happened to be located between her apartment and his place. As she grabbed her coffee off the bar, she quickly turned toward the door and slammed right into a hard chest. With an immediate apology, Elena looked up to find an extremely good looking hazel eyed man looking down at her. He quickly assured her that it was no problem but she would have to do one thing for him, go out to dinner with him. At first she was skeptical about the idea, but the sincere look in his eyes smoothed out any worry she initially had. Ever since that fateful morning, their relationship only blossomed.

That was up until a couple weeks ago. Elena was sure that she was developing feelings of love for her boyfriend, but recently she was getting mixed signals from him. He seemed to always be busy with work and could never fit in time to spend with her. Which is why Elena found herself in the company of Damon so often lately.

Oh and not to mention Mason definitely did not approve of Elena and Damon's extremely close friendship. Mason felt that best friends of opposite sexes should not have reoccurring sleepovers together. It seemed like every time Damon and Mason were in the same room together, both felt the need to claim their territory of Elena. It was like they were two male dogs peeing on her just to prove something to one another.

While Damon supported his best friend through every relationship she had throughout her life, he couldn't help but not approve of Mason. He always felt like the guy had a hidden agenda and took advantage of his Elena. Elena constantly pleaded with him to get along with Mason and just support her despite his apprehensiveness. So that's what he did...well at least attempted to do.

"You really would rather spend the day with that dog than with your bestest most gorgeous friend?"

"Damon, he is not a dog. I don't understand why you can't just accept him and the relationship I've had with him for the past 6 months. He's a really good guy and he takes care of me. You should appreciate that he is taking care of your best friend."

"Oh I could definitely take care of you just fine by myself" Damon said suggestively but in a joking manner.

Elena just rolled her eyes and ignored her best friend's comment.

"So can you take me or not? If not, I can just walk all the way across town in this very skimpy outfit and just hope that there aren't any scary, old, pedophile men walking around waiting for a poor innocent girl like myself for them to kidnap." Elena exaggerated.

"Alright, alright stop. You know I would never let you walk across town by yourself even if you wanted to. I'll go pay the check and I'll drop you off to your little lover boy."

Elena got out of her chair and walked over to Damon and planted herself in his lap and gave him a wet sloppy kiss on the side of his cheek "thankk youuuu Damon, you're the best."

"Yeah, yeah, don't you forget that."

"How could I ever? You're my main man."

* * *

Elena walked up to the familiar setting of her boyfriend's apartment clad in a white sundress and sandals, appropriate for the current summer heat. As she knocked on the door, her long waves bounced across her tanned back. After the first couple knocks she became a little frustrated. She made sure that her boyfriend's car was parked in the parking lot before reaching the apartment. Elena knocked three more times and waited as patiently as she could before she attempted to open the door herself. She was surprised to notice that the door was unlocked.

Elena opened the door slowly and walked through the threshold. She called out Mason's name and waited for a reply. With no reply, she continued to search the apartment. She heard movement in her boyfriend's bedroom.

"Hello? Mason, where are you?" She spoke hesitantly as she opened the door of his bedroom and let her eyes scan over her worst nightmare.

* * *

Damon walked into the well-known restaurant and approached the hostess stand. As he stood in front of the hostess, the young woman gawked at the Greek God like figure before her. Words escaped her as she stared into the endless ocean blue eyes knowingly gazing back at her.

He was accustomed to this type of reaction from women. He grew up dealing with this on a daily basis. Yes, many people called him a cocky son of a bitch, but only the people that were close to him, knew that he was quite the opposite. Under the physical appearance of Damon, he was one of the most sweetest, caring, and giving person anyone could ever encounter. His mother, Arianna, raised him to be a strong, humble, and independent man, and he would never let his confidence get too much into his head.

"Well hello there beautiful, do you think you can reserve a table for two for me?" He questioned the young woman and finished off with a wink in her direction.

"W-um-ye-yes of course..can-I mean, may I have your name?" The poor young girl stumbled on her words as he continued to stare back at her.

"Damon. Damon Salv-" He stated his name, but was interrupted by a feminine voice behind him.

"Salvatore" The female voice from behind finished. Damon turned around to find a slender, good looking woman, with long dark hair, hazel eyes, dressed in a tight red dress, and a pair of black sky high heels accenting her long, lean legs.

Damon let out a long whistle and walked up to the female. "Let me guess, Katherine Pierce?" He stated in his normal charming ways.

"The one and only." She responded in a husky, seductive tone while she scanned her eyes up and down the handsome man in front of her.

"Um, excuse me, Mr. Salvatore? Your table is ready." The young flustered hostess stated from behind.

"shall we Ms. Pierce?" Damon offered out his arm to woman and she hurriedly accepted the invitation.

"We shall." The couple walked towards the back of the restaurant and sat down.

After settling in their seats, Damon started the conversation. "So what's your story Miss Pierce?" Damon questioned as he wiggled his eyebrows and charmed her with his bright blue eyes. But before she could reply his phone went off in his jacket pocket. The ringtone he heard signaled that it was Elena. They set up distinctive ringtones for each other so they knew that if one of them was calling, it was important.

"Hold that thought Katherine. I'm so sorry, but I really have to take this." He pointed towards his phone and walked towards a secluded corned a few feet away from this table. He noticed that Katherine was slightly astonished at his behavior but he could care less about what she thought. With that he answered his phone, "Elena I know you miss me after not seeing me for a couple minutes but I told you I'm on a date, what's up?" As he finished his last word he heard sniffling coming from the other side of the line and he instantly went into protective mode. "Elena, baby, what's wrong?"

Those words were all it took for Elena to crack over the phone. All Damon could hear was her sobbing. Through the crying, he distinctively heard the four words that would make him drop everything in a heartbeat, "Damon, I need you."

He could barely make out the words through her blubbering, but he knew that whatever he was doing in that moment didn't matter. All that mattered was going to Elena and helping her through whatever was making her hysterically cry.

"Where are you? I'll be there in five minutes."

"My house" she continued to sob through the telephone and Damon quickly promised her he would be there as soon as he possibly could.

Damon frantically returned to the table where Katherine sat. "I am so incredibly sorry Katherine but my best friend needs me and it cannot wait another minute. I will call you and reschedule as soon as I can." He spoke while grabbing his wallet and throwing down a couple twenties

"Are you serious?" An extremely annoyed Katherine responded.

"Please take this and order something or go somewhere else to get a bite to eat. Once again, I'm so sorry." He barely finished his last word before he was zipping out of the restaurant and running toward his Audi parked in the lot. He didn't care that he almost ran over innocent bystanders in the crosswalk, or that he went through red lights, he had to be somewhere, and he wouldn't waste another second to get there.

He had to get to his girl.

* * *

He took the steps of Elena's apartment lobby by three's instead of waiting for an elevator to bring him to his best friend. He couldn't get to her door fast enough. As he reached her door, he pulled out the key to her apartment and let himself through the entryway. He immediately found her slumped up against the wall in her hallway, clutching her cellphone, and tears running down her heart-shaped face. His feet carried him to her sobbing body and sat next to her.

"Lena, honey, look at me, you got to tell me what's wrong." Her watery brown eyes met his deep ocean blue ones and his heart sank in his chest. Yes, he's seen her cry countless times throughout their lifetimes. He's seen her cry tears of laughter, of happiness, and occasionally of sadness, but he has never seen the tears of heartbreak stream down her face. He pulled his hand from his side and reached for her hand in her lap and intertwined their fingers. He gave her hand a reassuring squeeze to encourage her explanation.

"I walked in on him with another girl" Elena could barely finish the sentence when she cried even harder than before.

As soon as the words left her mouth Damon saw red. His jaw turned hard and all he could think about in that instant was beating Mason to a pulp. But as soon as he felt his best friend's head rest on his muscular chest, he was brought back to reality. He embraced her trembling body with his arms and let her soak his thin t-shirt with her salty tears. In order to calm her down he took his hand and stroked her hair and back.

Damon knew how this simple gesture was all it took for Elena to calm down. Even when she was a little girl, Miranda would stroke her hand softly through her daughters hair and it would immediately calm her woes. As the years went on, it continued to be the only way to make things right for Elena.

It might of been hours or minutes before Elena's trembling body calmed down. It was when Damon could hear the deep breathing of her sleeping body against his chest that he decided to move her to the bed. Carefully moving beside her, he lifted her up and carried her bridal style to her bedroom.

Once he reached the mattress he slowly put her down and slipped the covers over her body. He stood over her sleeping body and noticed that a lock of hair fell against her cheek. With a feather light touch he moved the piece of hair away and caressed her soft skin.

As he watched her sleeping body he thought about how broken she looked before she dozed off. All he wanted to do was fix it. But honestly, he had no idea how to handle this situation. In all the relationships she had during her life, she was the one to break them all off. This was her first heartbreak and he wanted to just take all the pain away.

The touch on her cheek caused her to stir from her sleep. Opening her eyes, she saw her best friend standing beside her bed. "You're not leaving are you? Please stay with me. I don't want to be alone." Elena stated in a panic. Those were the only words it took for Damon to move to the other side of the bed and remove his shoes. Slowly he laid upon the mattress and turned on his side to face Elena. Brown met blue and it was as if they were seeing into each other's souls.

"Damon, why did he not want me anymore?" If his heart wasn't already in his stomach, it definitely was now.

"Elena, I have no goddamn idea why anyone would do something like this to you. You don't know how hard it is for me to not go out this very second, find him and beat him to death. No one does this to my girl. No one."

"Is there something wrong with me?" This question took him back. How could anyone make her feel like this.

"Elena stop it. There is absolutely nothing wrong with you. You are the smartest, most beautiful, funniest, and kindest person I know. Don't let that jackass make you feel like this."

"You're just saying that because you are my best friend."

"No Elena, I'm saying it because it's the truth."

"I thought I loved him. I really did. I was going to tell him today. I was going to walk into his apartment, find him and give him a mind-blowing kiss and pull away and confess my love for him. But instead, I walked in on him with another fucking girl. Why did he do this? I thought I was doing everything right in the relationship." Her emotions surfaced once again and she couldn't control the words spilling from her lips.

Damon moved closer to her body and pulled her against him and just whispered, "Everything will be okay, don't worry I'm here. Hey, look at me." Elena moved her head to look at her best friend. Damon moved his hands to cup her face and stared into her brown doe eyes. "This is not your fault." He stated with conviction in order to prove his point.

Elena searched his blue orbs and before she knew what she was doing, her lips pressed up against his. Damon was taken completely off guard by his best friend's lips upon his, but then relaxed into the kiss. With eagerness, Damon responded to the kiss and before either knew what was happening, he was on top of her and their kisses were becoming even more heated.

He pulls away after feeling the gravity of the situation. "Elena, what are we doing? We have to stop."

"Please Damon, I need this. I need to feel something other than pain"

"Elena, I want to take that pain away, I really do. But, I can't have anything ruin our friendship."

"This won't ruin it. I promise. Nothing could ever come between you and me. Ever."

As her brown eyes met his blue ones, everything around them faded away and their lips met once again in a passionate kiss. Damon's hands roamed down her hips and pulled her closer to his body. His hands went lower and pulled her sundress over her hips and over her head. As her head rested back on the pillow and her dark chocolate hair fanned out across the pillow, Damon couldn't help but stare at the goddess below him. Her olive skin contrasted beautifully against her white lace panties and bra. Damon's hands followed his eyes and caressed her full breasts over the lace.

"God you're so beautiful." Elena pulled his face back to hers and kissed him fiercely. Her fingers found the hem of his cotton t-shirt and pulled it up over his muscular torso and discarded it on the bedroom floor. Running her hands down his abs she popped the button of his jeans and pushed them off his hips. With help from him, he was finally rid of all of his clothes except the black boxers that were hung low on his hips.

Reaching behind her back he unclasped the bra and pulled it off her arms. As their naked chests met back together, the heat in their lower bellies only grew. Their kisses became more heated and their wandering hands touched every surface on each other's undiscovered bodies. They both felt the need for each other and soon the remaining clothing was discarded.

His hand roamed over her full breasts, down her taut abdomen and parted her thighs. He teased her clit with his thumb and he could feel her wiggle from above. He placed his other hand over her stomach to prevent her from moving. He heard his name moan from her lips and decided that he teased her enough.

"Damon, I want you inside me."

"Baby, are you sure you want this?"

"Trust me, I'm sure."

He positioned himself at her opening and reached his hands towards hers and intertwined their fingers as they rested above Elena's head. With a small thrust, Damon entered Elena. At that moment, it seemed like the world stopped moving. He couldn't believe how good she felt. Better than anything he has ever felt before. Her warmth and tightness had him reeling. He felt her move from underneath him and he knew she was ready for it all.

He began moving slowly in and out and slowly picked up the pace. Her face beneath him was one he would never forget. Her skin glowed from the thin layer of sweat that accumulated from their quick pace. They found their rhythm like it was the most natural thing in the world. Elena pulled one of her hands free and moved it down his back, pushing him and encouraging to go faster.

Her name fell from his lips as his name fell from hers. All that could be heard was the soft moans and movement of their new found pleasure. It was as if the world around them stopped.

He could feel her approaching her oblivion and he was definitely seconds away from the edge. With that, he rotated his hips slightly so that he could hit deeper within her. She met him thrust for thrust and with one last movement, they both fell over the edge. "Oh God, Damon..."

"Holy shit" He breathed out from above her and pulled out of her warmth. Laying next to her, he brought his arm over his eyes to try and come down from his high. He could easily say that he never came so hard in his life. He needed a couple seconds to gain back him composure. He glanced to her face and realized she was in a similar position.

"Fuck Damon, now I know why every girl is so goddamn obsessed with you."

Damon's hearty laugh filled the room, "Well duh? What did you expect, that I gave them really good neck massages?"

"Oh stop" with a playful eyeroll, she moved her body underneath the blankets and laid against the pillows.

"That's not what you were saying a couple minutes ago" Damon sing-songed.

"See, I told you that this wasn't going to ruin our friendship. Now that I'm thinking about it, this could be more than a one time thing. I mean, I certainly enjoyed it, and I'm pretty sure you did too." She said as she rested her head against her hand propped up by her elbow.

"Oh I definitely enjoyed it" Damon replied with wiggling eyebrows.

"You see it's perfect, since I'm not getting any from another boy anytime soon, we could use our friendship for other...benefits...if you understand what I'm saying."

"I don't know Elena..these types of things never work out. I don't want to lose my best friend."

"You're right, but they never work because people get attached. We're already attached at the hip, only now sex is involved. Our friendship doesn't have to change at all. Let's just make some rules. You can date whoever you want, as so can I. As soon as we get into serious relationships we stop this."

"Okay..But as soon as it starts to change things between us, we have to stop. I need you in my life Elena, I can't lose you."

"Deal"

"So uh, you want to try this again?" Damon spoke seductively and started nipping at her earlobe.

The moan she responded with was all it took.

**Please review :)**


	2. Everybody Talks

**A/N: Hello again! I'm truly sorry for the long wait for the update. The past month has been crazy for me! Good news though, I graduate high school next week and I'm technically already on summer vacation..which means more frequent updates! I'm not going to promise anything though, but I will try my hardest to get the next chapter up A.S.A.P. Thank you so so so much for the reviews on the first chapter! I hope you enjoy this chapter!**

**Chapter 2: Everybody Talks**

_Hey baby won't you look my way_

_I can be your new addiction_

_Hey baby what you gotta say?_

_All you're giving me is fiction_

_I'm a sorry sucker and this happens all the time_

_I found out that everybody talks_

_Everybody talks, everybody talks_

_It started with a whisper_

_And that was when I kissed her_

_And then she made my lips hurt_

_I could hear the chit chat_

_Take me to your love shack_

_Mamas always gotta back track_

_When everybody talks back_

**_Everybody Talks-Neon Trees_**

While standing under the steady flow of water coming from the large shower head, she let her body relax and get soothed by the hot temperature against body. After a few moments of letting the sensation take over her, she grabbed the shampoo and slowly massaged it into her long chocolate locks. While closing her eyes she rinsed the suds out of her hair. As she finished up in the shower she heard the glass door open and before she knew it, she felt a hard body press up against her bear back. She felt her wet hair being pushed towards one side of her neck and shortly after, slow sensual kisses pressed up against the side of her jaw and neck.

"Damon, c'mon stop I have to meet my mom for lunch in an hour. No more of this funny business."

"Please Elena, just a quickie. You got plenty of time." He seductively whispered into her ear as the stream of water from the shower hit them from behind.

Elena was quickly getting hot and bothered and it wasn't from the scolding temperature of the water.

"No Damon, you know how my mom gets when I'm not on time. Besides I haven't seen her in weeks and we have a lot to catch up on." Elena countered as she stepped out of the steamy shower and reached for a towel to dry herself off.

"So in terms of "catching up" does the include telling her about you and me?" He said with a cringe from within the shower. Just thinking about his almost second mom knowing about his sex life made him want to hide under a rock and never come out.

"I don't know, I haven't really thought about it. I mean I do tell her everything, I don't think she would react too bad about this."

"Elena, our parents have dinner with each other practically every night. Don't you think if you told your mom about us they would take it completely out of proportion and end up planning our wedding over their nightly dinners?"

"Now you're just overreacting. If I tell my mom not to say anything, she wouldn't. Come on, you know how close my mom and I are. I guess if you feel that uncomfortable about me talking to her then I could just keep it to myself." She looked up at him with her doe eyes as he propped open the glass shower door and pulled a towel around his waist.

"Fine, whatever, do what you want. And don't look at me like that. You know once I get those puppy eyes in my field of vision, there is nothing you can say or do that I wouldn't agree to." Damon replied with a hint of annoyance.

"That's right Damon, never forget it!" She said as she grinned widely up at him.

The smile on Elena's face seemed to be reoccurring more often in the past couple weeks since she walked in on Mason. Damon didn't think that he would see that smile for a while. But ever since they started their arrangement it seemed like she was happier now than when she was with Mason.

"It's nice to see that beautiful smile again."

"It's all because you helped me through this. I honestly don't know what I would do without you Damon. Thank you. Not just for this, but for everything. I'm so lucky to have someone like you in my life."

"Lena, you're my best friend. There's nothing I wouldn't do for you." He said as he walked towards her and placed his hands on her slim waist. "You need me? I come running. I'm easy like that." He responded with a wink.

Elena rolled her eyes and smacked the side of his muscular bicep. "God Damon, why do you always have to ruin a special moment." She scolded but couldn't contain the smile from peeking out.

* * *

Her sandal wedges hit the pavement with grace as she walked towards the restaurant where she was meeting her mother. She settled in a casual black shirt dress and let her tresses fall naturally against her back. As her mother's figure appeared at the table on the outside patio of the restaurant, she picked up the pace of her steps.

It's been a couple weeks since she's seen her mother and she couldn't wait to be in her mother's arms. Ever since she was a little girl, she had an extremely close relationship with her. It was almost as if Miranda wasn't only just her mother, but her best friend.

"Sweetie, aren't you just glowing. That Mr. Mason Lockwood must be taking care of you." Her mother embraced her in a warm hug and pulled back to show her daughter a playful wink.

While Elena inwardly cringed at hearing the bastard's name, she realized that her heart didn't drop. That familiar twinge of heartbreak no longer plagued her; thanks to her best friend.

"Actually mom, that's a topic we definitely need to catch up on."

"What do you mean? Last time we talked it sounded like you and Mason were getting quite serious."

"Yeah well, that's what I thought until I walked in on him fucking another girl." Elena's eyes fell to her hands that were placed on her lap. For the past couple weeks she was finally able to realize that what she had with Mason wasn't real love, it was "puppy love". She was in love with the idea of him than actually being with him. She loved his charm and handsome looks, but as she looked back on their relationship, she didn't find that real spark she craved. However, while she was positively over the jackass, she couldn't help but still feel like a failure.

"Oh honey, why didn't you call me and tell me?" Miranda reached for Elena's hands from across the table. "If it makes you feel any better, I was always on Damon's side of not liking him."

Elena felt the sides of her lips tug upward.

"Trust me, I'm on your guy's side now too."

"I hope that Damon took care of the asshole."

"Well..he was a little too busy with me." Elena couldn't help the blush that rose up in her cheeks.

Miranda was completely oblivious to her daughter's sudden change of color and responded with "Yeah, I can only imagine Damon not wanting to leave your side until he was completely sure you were feeling alright."

"Oh he definitely made me feel better." Elena was so close to giggling at the double meaning of her words, but she remembered Damon's apprehension about her telling her mother about their new arrangement. However, Elena couldn't keep anything from her mom and she was so close to just coming out with it.

"Good I'm glad sweetie. You know, that boy has been their by your side from when you were little babies. You guys were and still are inseparable. But I'm glad you have him in your life. It's nice to have that reassurance that someone is looking after my baby."

"Mom, I have to tell you something but you have to promise me to not tell a soul. Don't tell daddy and especially don't say anything to the Salvatores. This is between you and me. I'm channeling the mother/daughter swear to secrecy bond right now."

"I don't know whether I'm more intrigued or scared about what you are going to tell me. But of course Elena, if you ask me to to say anything I would never."

"Okay, well after I walked in on Mason I was a complete mess. I couldn't stop crying and now that I'm looking back on it, I don't even think it was because Mason wasn't my boyfriend anymore. It was more because I felt like I was worthless. Seeing him with another woman made me feel like I wasn't good enough. So I called Damon and told him to come over."

"Sweetie, you will always be good enough. He is the one that wasn't good enough for you. Any man that makes you feel like that isn't worth a second of your time."

"I know. I mean, I know that now. But at the time I just felt so insecure and I just needed someone or something to make it better. So when Damon came over he just held me and comforted me. It was making me feel a lot better than before but I still felt like shit about myself. So we were laying in bed together and he was just saying everything I needed to hear and then next thing I know, I'm kissing him. Kissing turned into more and then I was telling him that I needed him to take the pain away. Then one thing lead to the other and we slept together." Elena was afraid to look up at her mother but then she heard the soft exhale come from the other side of the table and Elena looked up.

"I'm not going to say I didn't see this coming, I was just waiting for the day to come. Well what happened afterwards?"

"You mean you knew that one day we would sleep together?" Elena shot up her eyebrows as she waited for her mother's reply.

"Elena let's be real about this for a moment. He isn't too hard on the eyes, to say in the least, and well you, you're my gorgeous little baby. You guys spend almost every second with each other and you two are very passionate about each other. I'm surprised it's taken this long!"

"Mom, that is kind of weird that you knew all along that this would happen. But I guess you make some valid points."

"You never answered my previous question. What happened afterwards? Was it awkward?"

"Well before we went all the way Damon was really apprehensive about it, he didn't want to let anything affect our friendship.

"That's my Damon." Miranda smiled just thinking about how her best friend Arianna raised her son into a gentleman. Of course he was a little rough around the edges and cocky at times, but he truly knew how to treat a girl. Especially when that girl was Elena.

"I mean, I completely agreed with him, nothing in the world is worth giving up our friendship. But after, it wasn't weird at all. It was as if nothing changed between us or between our friendship. The only thing that changed is that we got an added bonus of sex. Mom, it felt so right. I don't even know how to explain it but it didn't feel wrong, not at all. So we made an agreement to be "friends with benefits" I guess you could say. I know, I know these things never work out but that's why we put some rules to it. We both can date whoever we want and once we start seriously dating someone, then we stop it. I really believe this can work. I mean, it's made me feel so much better in the past couple weeks and it seems like our friendship has gotten even better." She sighed in relief after putting it all out there for her mom to comment on.

"Well you know I'm going to support any decision you make in your life, but sweetie, I'm a little skeptical on this one. I trust that you have thought about this, but this could end really badly. It's hard for me to accept the fact that this could ruin your friendship with him."

"Mom, trust me, we're both adults and understand each other more than anyone else. If things start getting weird, then we'll stop it immediately. I know this can work and besides look at how much it's helped me in the past couple weeks."

"Alright Elena, I just want you to be careful. I love you two very, very much, and I just want the best for the both of you."

"Thank you mom, I know this will work. Nothing bad is going to happen."

"Okay, that's enough talk about that. Tell me, how's the writing going."

"Ahh..the writing, about that."

About 2 years ago, after graduating from Columbia with a master's degree in creative writing, Elena considered writing a young adult novel. After a year of developing the foundation of her story, she approached a publishing house. Before she knew it she had a book deal and a very large advance in her bank account. However, in the past couple months she began losing her passion for her story. She didn't know what was wrong, but she couldn't formulate the words she needed to get down. She only had a couple chapters left to complete. All in all, her editor was not happy in the slightest.

"What's wrong Elena?"

"I don't know mom, I guess I'm just having writer's block and I can't seem to shake it. Every time I sit down and try to write, nothing comes out."

"Maybe it's time you get back into weekly yoga sessions, I remember how much it helped you in college. I think you just need to relieve some stress. I know you Elena, not being able to write is only making you stress out more. You need to find some inner peace."

"That's a good idea mom. I just hope it helps. I can't stand this feeling. I have my editor down my throat for the next part of the story and I just feel like I can't do it. What if I can't deliver what is expected from me? Sometimes I feel like I can't be the writer I always dreamt to be. I'm already 26 years old, I thought I'd already have a novel published by now"

"Elena, listen to me. You need to stop doubting yourself in everything you get involved with. You need to be the strong and confident woman I raised you to be. I know she is in there somewhere. You need to let go of all this, maybe you should take a nice vacation somewhere with Damon. I think that will do the both of you good. He's too into his work. You both need to go somewhere tropical and heal. I know you two will be able to do that together."

Elena sighed, "Yeah, I'll talk to him about it and see when his schedule at work opens up."

"Good, now let's dig in. I'm starving." Miranda smiled.

* * *

Her hands held the silver drink shaker as she moved it back and forth and continued to then poor the neon pink liquid into a martini glass.

"There you go, enjoy." Elena flashed her perfect smile to the patron in front of the bar.

"Thank you!" The woman replied.

A few feet away from the bar she spotted two familiar faces that instantly brightened her day. The two bodies moved closer until it reached the space of bar right in front of Elena.

"Well hello most beautiful bartender that has ever walked the face of the earth." Damon playfully greeted her.

"Oh brother, stop kissing ass. We all know you are her favorite." Stefan stated from behind as he walked up to stand next to Damon.

"Very true brother, very true."

"What can I get you two handsome boys?"

"The usual." Damon and Stefan responded together.

Elena laughed out loud at their twin-like tendencies. "Okay, coming right up!"

After grabbing the drinks from Elena, the Damon and Stefan found a table in the back corner away from all the hustle and bustle of the Friday night crowd.

"So brother, tell me what's new in the exciting life of Damon Salvatore." Stefan asked.

"Oh you know, making panties drop here and there." Damon replied as he wiggled his eyebrows. "Actually, there was something I wanted to talk to you about. But before I say anything, I would like to add a disclaimer..it wasn't my idea."

"Well this shall be good..."

"Please don't tell anyone. And by anyone I mean your little Barbie girlfriend."

"Alright, alright. Just spit it out." Stefan spoke as he brought the brim of his glass to his lips and let the liquid enter his mouth. He felt like he alcohol in his system to prepare him for what Damon was about to say.

"Elena and I started to sleep together..."

Damon was answered with a spray of bourbon coming from his brother's mouth. After wiping away the liquid on his face, he looked into his brother's shocked green eyes.

"You got to be fucking kidding me Damon. I mean let's be real Damon, you've made a lot of stupid decisions in your life, but I'm pretty sure this one takes the cake."

"Let's refer back to that disclaimer I inserted before. It wasn't my idea."

"I find it really hard to believe that something involving sex wasn't your idea."

"Okay fine, clearly you don't believe me. So let me start from the beginning. Long story short, Elena walked in on the dog a.k.a Mason fucking another girl, she was heartbroken, I picked up the pieces, she wanted me to put the pieces back together by sleeping with her. I hesitated because, well, she's my best friend man. I can't have anything ruining that. I would be absolutely nothing without her. I mean, of course I have you and everything but she's Elena...my Elena. But she kept reassuring me that nothing would change. So I gave in. And she was right about our friendship not changing. Everything is exactly the same as it was before, except better. Right now I am one happy fucking man, my job is great, I have the best family, a beautiful best friend, and I'm getting laid every day. How fucking awesome is that?"

Stefan shook his head, "Damon, I'm going to tell you what I think about all of this but after I'm done, can we never talk about Elena and you sleeping together. I would really appreciate not having the image of my almost sister getting it on with my brother."

"Deal. As long as you never associate Elena as your sister because that would make her my sister and after what I've been doing with her for the past couple weeks, I definitely don't associate her as a sister."

"Are you sure about all of this? Damon... this can end extremely bad."

"All joking aside, I completely understand where you are coming from. Trust me, that's why I'm talking to you about this. I need your brooding mind to help me out with this."

"Alright talk to me, what are you thinking?"

"Well we have these rules...we are allowed to date other people and if either one of us get into a serious relationship, we stop sexing it up."

"I don't know about this Damon.."

"Stef, you didn't see her after the whole Mason thing. She looked so completely broken. She was saying all these things about how she felt like she wasn't good enough and then she looked at me with her big doe eyes and my mind went to mush. But after we did it, she looked like she was completely fine. She's been so happy recently and I'm glad that I put the smile on her face. I can't just stand there and watch her hurt. I had to do something and I know it could completely blow up in our faces but at the same time, I don't want to end it. To me, it's easy. I don't have to deal with a nagging girlfriend and a messy relationship"

"I just want you to be careful Damon. I know you have rules and everything but there is a lot more on the line than just your relationship with her. If anything happened between the two of you, it would involve the whole entire Gilbert/Salvatore clan. And you guys are best friends..."

"You're right, which is why I'm just going to take it day by day and make sure my beautiful best friend keeps that smile on her face."

"So uh, speaking of beautiful girlfriend...I kinda wanted to talk to you about something as well." Stefan smiled.

"And what would that be?"

Damon watched Stefan reach into his leather jacket's pocket and pull out a small black box.

"Well, I think I'm ready to take the next step with Caroline."

"You think?" Damon picked up the small object and opened it carefully. "I hope you know! This is fucking huge!" Damon's blue eyes took in the 5 carrot diamond in front of him.

"No, I'm definitely sure I'm going to do it. I just don't know when. Well, I have a couple ideas."

"Wow bro, congratulations. So this means Barbie is now my sister-in-law...great."

"Well that's if she says yes."

"Oh don't worry, after taking a look at this baby she will not be able to say no. How are you thinking of asking her?"

"You know how she is so obsessed with that band Florence + The Machine...Well, there is a concert coming up. It's at the outside venue she and I met at in Upstate New York. I thought that you and Elena can tag along and we can make a mini vacation out of it and I'd pop the question during their set."

"Very corny. I like it."

"Really? I mean I know it's not some romantic rose petal pathway kinda thing but the place is special to us and she loves Florence so I figured it'd be perfect."

"I'll talk to Elena about it and don't worry, I'll make sure she keeps it on the DL.." Damon smirked. As the words slipped from his mouth, a slender brunette appeared from the corner of his eye.

"Keep what on the DL?" Elena questioned as she approached the two men sitting at the table. Her eyes caught a glimpse of the large sparkly diamond placed in the velvet black box and her curiosity peeked. "Oh my god, what is that?"

"Elena, what does it look like?" Damon asked with a smart ass attitude.

"I know what it is but who is it for?" Elena rolled her ! You're proposing to Caroline?"

Damon's blue eyes met with Stefan's and gave him a pointed look to explain. Stefan preceded to say, "Yes, Elena, I plan on proposing to her sometime soon.."

Before Stefan even finished his sentence Elena jumped into his arms with excitement. "Stefan, oh my goodness, this is so amazing. Wow, this ring. It's so perfect for her, she is going to love it! When are you going to do it?" Elena rambled excitedly.

"God, you'd think you just told her the ring was for her." Damon said jokingly.

Elena just rolled her eyes. "I'm just excited for Caroline and Stefan."

As Elena's brown eyes scanned the ring she was surprised to feel a pang of jealousy. Of course she was absolutely thrilled for her close friends, but she always imagined herself married with a baby on the way by the time she was 28. All of her self doubt came bubbling to the surface as she realized that she was no where near getting married or having a baby anytime soon.

"Well can you please keep this between us, I know how it goes when you two get together. There's no filter..." Stefan stated.

"Don't worry Stefan. Have some confidence in me." Elena replied with a teasing smile

"I do, I do. I just want this to be perfect for Caroline...So here's the plan. I was just telling Damon about how I'm going to pop the question at the Florence + The Machine concert in a couple weeks. The concert is at the venue where we met and you know how obsessed she is with that band, so I figured it would be the perfect place!"

"Ohhhh, I love it! She is going to love it!...Now I suggest you put that ring away before she comes waltzing in here. She told me she was going to stop by."

Stefan quickly placed the ring box in his jacket pocket as he saw a familiar head of blonde curls coming towards their table.

"Speak of the devil." Damon stated with a lopsided smile. He loved getting a rile out of Caroline. He watched as the blonde woman hugged Elena tightly and moved to his brother's embrace.

Even though Damon and Elena were best friends, Caroline has always been Elena's go to girl. Of course she had Damon, but Elena needed her girl best friend for things that Damon could simply not understand. It seemed like whenever Damon and Elena were not together, Elena was with Caroline.

"Well if it isn't my boyfriend's bonehead of a brother...Oh, I mean, hi Damon," Caroline countered, while giving Damon the stink eye.

"Can you two get along for at least 2 seconds?" Stefan pleaded.

"No." Both Caroline and Damon replied together.

"Come on Damon, I need a drink. Caroline would you like anything?"

"Sure, the usual. Thank you best friend!" Caroline responded.

With a smile, Elena grabbed Damon's hand and moved towards the bar to get drinks for everyone.

As Damon and Elena reached the bar, Damon leaned in to whisper something in Elena's ear and she giggled in response. From an outsider's perspective, it looked as if they were a couple in love, with their flirty gestures and loving stares. Caroline's suspicious eyes even caught on to what was occurring between her two friends.

"Stef, what's going on with Damon and Elena?"

Stefan almost spit out the sip of bourbon as he heard Caroline's question.

"What do you mean what is going on with Damon and Elena? Nothing is going on with them. Why would you think something is going on?" Stefan nervously rambled. Even though Caroline was his girlfriend (hopefully soon to be fiance), he wasn't sure if his brother wanted Caroline to know his business.

"I don't know, look at them. They are extra touchy feely tonight. More than normal..." The blonde said.

Stefan glanced at the bar where Damon and Elena continued to flirt.

"Oh that? That's normal...You know them."

"I guess. It just seems like they are more touchy-feely than normal..wait a second!..Do you know something I don't know?"

Stefan tried to avoid is girlfriend's interrogating stare by looking anywhere but her pointed stare.

"Wha-what? No!" Stefan tripped over his words and he knew he was a goner.

"You do know something! Tell me!"

"Caroline, stop I don't know anything!"

"Fine, if you don't tell me, no sex for a week!"

"Ugh Caroline, don't do this to me! Why don't you go up to your best friend and just ask her? I'm sure she will tell you."

Caroline rolled her eyes at her boyfriend, "You're useless. Fine, I'll be back.." She stated as she confidently walked towards Elena. Her best friend had some explaining to do...

**A/N: Reviews are love :)**


	3. Only Wanna Give It To You

**Chapter 3: ****Only Wanna Give It To You**

_Cause I only wanna give it to you_

_And I want you more than a new pair of shoes_

_I only wanna give it to you_

_And I sure do hope that you feel like I do_

_Can't let this go what can I say?_

_I just don't know_

_My love ain't no trip for the weekend_

_Here to stay for all of the seasons_

_You're the weakness that I can't control_

**_Only Want To Give It To You- Elle Varner Featuring J. Cole_**

The brunette beauty felt someone tap her shoulder as she stood by the bar waiting for her drinks. She curiously peeked over her shoulder and was surprised to see her blonde best friend casting a squinty at her. Elena noticed that her stare was not looking directly at her, but the unusual closeness between her and Damon's bodies as they stood together against the ledge of the bar. Caroline's interrogating blue eyes met with Elena's curious brown eyes.

"What's up Care?" Elena asked curiously. What was wrong with her best friend?

Caroline replaced her harsh glare with her normal bubbly persona and sweetly said, "Elena, may you please join me in the bathroom?"

"Hold on a sec, let me just help Damon bring the drinks back to the table."

"Oh I think he can do it just fine by himself, right Damon?" Caroline responded giving Damon a pointed stare. Elena looked up at Damon with a confused expression. She couldn't keep up with Caroline's whiplash personality.

"Uh yeah sure, go ahead...do your little girl thing with Barbie."

"C'mon Elena." Caroline grabbed Elena's arm and pushed her through the dense crowd in the club. When they finally made it to the ladies restroom, the blonde pushed open the door and quickly ushered her best friend inside.

"Caroline what is your deal? Why couldn't you wait a minute?"

"I think I should be the one asking questions, not you..."

"What are you talking about?"

"Don't play dumb with me, you and I both know that there is something fishy going on."

Elena paused at her friend's words. She felt a wave of nervousness wash through her. She hoped with every fiber in her body that Caroline didn't find out about Stefan wanting to propose to her...She would just have to continue the dumb act.

"No Caroline I don't know...please fill me in."

"Oh come on! I saw you and Damon by the bar. You might as well of just stuck your tongues down each other's throats."

"Wha-Damon? Damon and I?" Relief washed through her before she could process what Caroline was trying to explain to her.

"No Damon and Helga...Yes, you and Damon."

"You know how Damon is, he gets like that sometimes." Trying to avoid where the conversation was going.

"Yeah I know that, but this was the first time I saw you equally reciprocate the weird best friend PDA."

Elena contemplated what to say next. Of course she wanted to tell her best friend everything but she would rather do it when she wasn't intoxicated and in a bar bathroom. Luckily, Caroline's phone went off and distracted her from pressing any more information from Elena.

"You're so lucky Stefan wants some right now, or else I would press this more."

"Okay ew, please don't talk about your sex life with Stefan around me. He's like my brother."

"Yeah, yeah whatever. We are meeting tomorrow for breakfast, no excuses, And I will get you to tell me what you are hiding..."

Elena giggled at her best friends persistence. "Okay, Caroline. See you tomorrow morning." She watched the blonde retreat from the bathroom. Once she was gone Elena turned towards the mirror and took in her flushed face. Running her hands under the cool water she brought them up to her warm face in hope to cool down. Moving her hands through her thick brown locks, Elena took a deep inhale and shakily released the air. Speaking to no one in particular she muttered while shaking her head in her hands, "She is going to flip the fuck out when I tell her..."

* * *

"YOU'RE WHAT?" Caroline's blue eyes shot open as her loud voice carried out through the outdoor patio of the restaurant her and Elena were currently seated at.

"Shh! Caroline! We are in a restaurant, you can't just scream like that!" Elena tried to reason.

"I'm sorry, but I think I just heard you tell me that you are sleeping with Damon?" The blonde completely disregarded Elena's previous statement and continued on.

"Yes Care, Damon and I are sleeping together."

"And you are not "together" just friends with benefits."

"I guess that's what people call it."

"It's also how people ruin completely solid friendships."

"I know okay. But trust me, it's good. We are being careful about it."

"But isn't it weird? I mean he has been your best friend since practically birth."

"It's hard for me to put it into words...it just feels right. I mean it is just sex, it hasn't changed anything between us."

"Except for the fact that you two love each other." Caroline bluntly stated.

"Of course we love each other, like you just said, we are best friends."

"No Elena, what I mean is that the both of you are IN love with each other. Which is why you feel so comfortable having sex with him and vice versa. This whole 'friends with benefits' thing works for you guys because it allows you to be together without feeling vulnerable in a real relationship."

Elena couldn't believe the words that came out of Caroline's mouth. Never has she ever considered that perspective and she wasn't ready to even comprehend it anytime soon. "That's absolutely ridiculous. Trust me, we are not in love with each other."

"Keep telling yourself that Lena. Look, I love you, you're my best friend and I wouldn't be saying this if I didn't want the best for you, but sometimes you are completely oblivious to what is right in front of you. I mean, have you even been on a date since you started this thing with Damon."

"Well no, but Caroline it's too soon for me to start dating again."

"Too soon to date but not soon enough for you to jump in Damon's bed?"

"Okay that is totally not the same thing."

"Yeah okay Lena…But didn't you say that you would stop your arrangement with Damon once you started a serious relationship? Well how are you supposed to move on to the next relationship without dating? Look I'm not telling you to go find 'the one' but you're almost 27 and this isn't the time for you to be wasting time with a fuck buddy…even if it is your best friend."

"But-"

"And I'm going to go out on the limb and say that Damon hasn't been out on a date either...Do you see what I'm saying?"

"You're wrong Care, maybe we just haven't found people that we are interested in.

'Yeah maybe because you guys are too busy going at it like bunnies and too scared to admit your true feelings about each other.' Caroline thought in her head and instead replied, "Okay Lena. Whatever you say." Knowing it was sometimes easier to just drop the subject.

"Thank you, glad we can move on."

As they continued on with their breakfast, the mood switched back to their comfortable best friend banter. Caroline noticed out of the corner of her eye, at a table several feet away, a handsome brown haired, brown eyed man sneaking glances at Elena. Intrigued by the gorgeous man ogling at her best friend, Caroline took the initiative to tell Elena about the admirer.

"Hey Lena" Caroline whispered from across the table and waited for Elena's eyes to meet hers. "See that hottie" her blue eyes quickly pointed towards the man several feet away "he hasn't stopped looking over at you." Elena followed her best friend's eyes and caught a glimpse. Her cheeks turned a deep crimson as she noticed the man was indeed looking at her. Her sudden embarrassment didn't go without notice by the brown-eyed man. As Elena snuck one more glance at him behind the curtain of soft waves falling around her face, she saw a 'panty dropping' slanted smirk gracing his gorgeous face.

"Yeah he's pretty handsome but I don't know Care..." Elena said uneasily

"Well, you better figure something out because here he comes."

"What?" Elena's heart rate spiked as she saw the man walking directly towards her table still wearing that adorable smirk.

When he reached Elena and Caroline's table, his smirk remained on his lips and spoke, "I don't mean to sound creepy but I can't take my eyes off you. You are absolutely gorgeous. My name is Kol." He introduced himself in his seductive Australian accent while reaching out with his hand to take Elena's in a handshake.

Elena politely smiled and shook hands with the stranger. "Well thank you Kol."

"May I ask what your name is beautiful?"

"Elena."

"Elena..." Kol let her name roll off his tongue, "I know this may seem extremely forward... but I can't leave here without asking for your number and a proper date."

The brunette felt her cheeks redden with flattery and quickly stole a wary glance at her best friend across the table. Elena could see Caroline's excitement all over her face. Returning her gaze back to the handsome man in front of her, she took in the man before her. He looked to be around her age, fairly tall, and his messy dark hair matched his deep and luring brown eyes. All in all, he was very handsome, and the accent was only a plus.

From the corner of her eye she could see Caroline's head bobbling up and down frantically, encouraging her to say yes. As quickly as she started to consider the young man before her, she felt her walls come up around her. Something in her head was preventing her from saying yes. She wasn't ready to start seeing anyone right now. Even though she was sleeping with Damon pretty much every night, she didn't want to have to handle the complications of a relationship...even if it was just one date.

"Kol, that's really sweet of you, but I just had an ugly break up and I don't think I'm ready to start dating yet."

Disappointment filled Kol's face but he quickly recovered. "I understand" He replied with a nod. "But hey, let me at least just give you my number and when you feel like you are ready, you can call me." He responded with a sense of hope in his voice.

Elena smiled politely at Kol, "Yeah of course" she pulled her phone out of her bag and handed it to him so he could enter his number.

"I'll be waiting for the call, Elena." Kol playfully winked before turning back towards his table.

After watching him retreat back to the table, Elena looked at her best friend from across the table, a fuming best friend at that.

"Please tell me I just heard wrong. Tell me you did not just say no to him."

"I could say that, but then I'd be lying..."

"Elena Gilbert, why did you say no?"

"Like I have told you a million times today, I am not ready to get back into the whole relationship drama. What don't you understand yet?" Elena was starting to get frustrated at her best friend. She spent the better half of their lunch date explaining to Caroline why she has not begun dating yet.

"He wasn't asking for a long-term relationship! He was just asking for one simple date. Probably some cliche dinner and movie date!"

"Caroline, I still feel like it is way too soon for me." She responded with an edge in her voice.

"Like I said before, it's too soon for you to go on one date with a new guy but it's not too soon for you to hit the sheets with Damon?"

Elena couldn't hold in her frustration any longer.

"You know what Caroline, I love you and you are my best friend. I also know that you are just helping me out here and want the best for me, but what I do and who I do it with is none of you business to comment on! This is my life and I am going to do whatever the HELL I want to." With that, Elena picked up her purse, pulled out some money, left it on the table, and walked out of the restaurant.

* * *

His blue eyes followed the bustling activity on the street below him as he looked out his floor to ceiling window in his spacious New York City office. As a venture capitalist for the largest venture capital firm on the eastern seaboard, it was safe to say Damon was living the good life. As one of the youngest VC in the firm, he was also the most successful. He was more than just good looks, Damon had a keen eye for profitable endeavors and was extremely smart. He could probably retire at this very moment and be set for the rest of his life, without a worry in the world about money.

His attention turned from the activity below him to the sound of his office door opening. Stefan and Alaric walked through and sat at the chairs in front of his desk.

Alaric has been Damon's best friend besides his brother, Stefan, since high school. The three of them are more like brothers than friends and can always count on each other. Alaric went to college with Damon and Elena and wound up working in the same firm as Damon. Alaric, also a successful Venture Capitalist, is dating Meredith Fell, a girl he met while at college.

"Well hello, brother and my dear drinking buddy." Damon greeted the men. "I don't mean to be rude but why are you here Stef?"

"Though I'd just stop by and see how things are going."

"In other words..."

"Still benefiting with Elena? Is what your brother means." Alaric cut in before Stefan could say anything.

"Seriously. You come interrupt me at work to ask me something that is none of your business?"

Alaric cut in once again, "I don't even understand how you can do that with Elena. You two are so freakishly close like brother and sister, how can you feel comfortable doing something like that?"

Damon pinched the bridge of his nose with his thumb and index finger in annoyance. "Don't. Call. Her. My. Sister."

"He doesn't like it when we refer to Elena as his 'sister,' considering, I quote from him, 'the things he's done to her.'" Stefan explained to Alaric.

"Okay, so why don't you just ask her out on a date already? Alaric asked Damon.

"And why would I do that..."

"Oh Damon, Damon, my brother. You are smart, but sometimes you can be so incredibly stupid. C'mon we all know what's going on here. Your into Elena as more than just a best friend. It's completely obvious. Even Elena feels the same way, the both of you are just too scared to admit it. But frankly, we're all tired of watching this going on. You guys are just dancing around your feelings and getting into this stupid friends with benefit situation that is just going to make things worse."

"Elena and I are just friends. Best friends. I don't know what feelings you guys are talking about but we are just best friends, nothing more. I would do anything for her, which is why we are in the friends with benefits situation."

"Okay, then what about that girl that asked for your number at the bar a couple weeks ago? She was pretty hot!" Alaric questioned.

"Oh god." Damon groaned. "I wasn't even into her. That girl was so annoying, she kept talking and talking. I only asked for her number so I could shut her up and get the hell out of there."

"You haven't been into anyone since you started this 'Elena with benefits' thing. Don't you think that is telling you something..." Alaric pressed.

"That's not true! I went on that date with that Katherine girl recently."

"You mean the girl that you walked out on in the first five minutes of your date to go see Elena?" Stefan questioned with raised eyebrows.

"Hey now, she desperately needed me. I wasn't going to just let her bawl her eyes out to me on the phone and tell her she had to wait for me to finish my date."

"Yeah, yeah whatever. So have you called Katherine back to reschedule?" Stefan asked curiously.

"I've been meaning to, but I have just been caught up with work and everything."

"Everything being Elena."

"I kinda have to agree with hair boy on this one, Damon…" Alaric spoke.

"Seriously guys? That's enough. You're really starting to piss me off. How many times do I have to tell you that Elena is my best friend and I just haven't found anyone worth my time yet. That's it! Can we drop the subject already?"

As Damon's blessing in disguise, Stefan's phone began vibrating loudly against the desk.

Answering his phone, Stefan heard Caroline's frantic rambling. "Woah, Caroline slow down! What do you mean Elena just left you in the middle of lunch?" Stefan asked gently.

"Oh god, what did Caroline do now." Damon groaned.

After stepping out of the office, Stefan listened to Caroline's explanation. "I might have pointed out to Elena that she is not ready to start dating again but yet she is ready to jump in Damon's bed every night. I didn't mean for it to come out so harsh but I just couldn't hold it in."

"How do you know she isn't ready to start dating again?" Stefan questioned not really understanding why Caroline would bring it up.

"This guy approached Elena while we were eating and he was absolutely perfect for her, well from what I could tell, and he asked to take her out on a date." Caroline rambled.

"Seriously? He just walked up to your table and asked her out?"

"Yup. I mean he was extremely forward about it but he was extremely good-looking and well mannered. And the best part was that he had an accent! " She replied.

"Well what did Elena say after he asked her?"

"She kindly said no, but at least she got his number. I doubt she'll actually call him."

"Wow. I mean it was just one date, I'm surprised she said no." Stefan couldn't believe it but at the same time he knew exactly what was keeping Elena from accepting the date…Her love for Damon.

"Exactly my point! She told him that she wasn't ready to start dating because she just had a messy break-up. He said that he understood but you could totally tell that he was disappointed as he walked away. That's when I hit my snapping point and totally freaked out on her."

Stefan groaned, "Caroline, I love you but why did you have to snap at her. You know how Elena gets!"

"I didn't mean to upset her, I just can't stand to watch what she's doing. She either needs to get back in the dating game or finally admit that she has feelings for Damon. But as Elena told me, it's her life and her business."

"I know babe, I know..Trust me. I basically just did the same thing to Damon and reacted just as bad. But I think what we need to do is just be there for the both of them. They're going to do what they want to do regardless of what we say to them. And Elena was right, it is her life and her business…same goes for Damon."

"You're right…I guess constantly telling them what they should and shouldn't do is only going to push them away from us."

"Care, how about we take a break from all this and go hang out at my place and chill for a little while."

"I don't know, I need to go apologize to Elena, Stefan."

"And eventually you will. But you have to give Damon time to talk to her and calm her down. You can go visit her later and apologize. Alright?"

"Yeah, okay." Caroline responded.

"Let me go back inside and tell Damon to go talk to her."

"Alright, I'm driving over to your place now."

"Okay see you soon."

"Hey Care?"

"Yeah?"

"I love you."

Caroline smiled wide, "I love you too, Stefan."

Stefan walked back inside the office and Damon immediately question him. "What happened?"

"Well it seems like Caroline might of gone off about your guy's arrangement and Elena got pissed at her and stalked off."

"Typical Caroline…" Damon mumbled. "Now, let me guess, I have to go fix Barbie's damage?"

"Yeah, I think it would be best for you to go talk to her and calm her down. She says that she didn't mean to upset her, it just came out harsher than she intended."

"Obviously." Damon picked up his belongings and exited his office.

* * *

Damon gently knocked on the door of his best friend's room and before entering the bedroom. Walking through the doorway, he immediately caught Elena's eyes and gave her a small smile. She barely returned the smile before saying, "Hi."

"I've been looking all over for you. You're a difficult girl to find, Elena Gilbert. Were you here all along?" Damon asked while approaching her bed and laying next to her.

"Yeah" she sighed and set down the book she was reading on the night stand next to her bed.

"Want to talk about what happened with Caroline at lunch today?" Damon asked gently.

"Some guy asked me out while I was at lunch with her." She spoke softly while moving her eyes to gage Damon's reaction.

"And did you accept the offer?" Damon waited for her answer, unsure whether he wanted to know the answer. _Why do I care so much if she went out with another guy..._

"I said no."

Damon released the breath he was unaware he was holding. "Oh…Well how does this relate to the fight between you and Caroline?"

"Well I told the guy that I wasn't ready to start dating because I just had a messy break-up and that caused Caroline to freak out. She doesn't understand that I'm not ready to put my heart out there again. I mean I thought I really loved Mason…and look how that turned out. I was completely wrong about him…I can't imagine getting so close to someone, thinking you know a person so well, and then a split second everything turns upside down. I don't think I can go through that again anytime soon. But of course Caroline has to throw our arrangement into my face. It's like she thinks that just because she doesn't agree with it, I can't do it. I just couldn't hold my frustration in and listen to her bash my personal decisions, so I just got up and left."

"You had every right to be upset, Lena. Don't listen to Caroline, you know how crazy she gets. Sometimes she completely forgets about other people's feelings. It's your life and you can do whatever you want to do. Do what makes you happy, not what everyone else approves of."

"Yeah, that's basically what I told her.."

"Good, I'm proud of you Lena. You stuck up for yourself against the big bad Caroline." Damon playfully winked at his best friend in order to lighten the mood.

Elena softly smiled back at him. A comfortable silence ensued between the pair as they sorted their own thoughts before Elena broke the silence.

"Do you ever wonder if we are missing out?"

"What? Missing out on what?"

"Dating. I mean do you think our arrangement is preventing us from seeing other people. I know we have our rules about dating whoever and whenever we want but you haven't been out with any girls and I haven't been out with any guys…maybe Caroline is right, maybe I should start dating just to move on from Mason…"

"Hey now, don't second guess your instincts. If you don't think you are ready to date then don't." Damon hoped that he didn't sound to obvious about not wanting her to date other men. It's not that he didn't want to share Elena with anybody else, well, maybe that was part of it, but he didn't want to see his best friend go through another heartbreak. "But to answer your question, I don't think we are missing out. I think we are just being extra picky about who we let into our lives and our hearts. There's absolutely nothing wrong with that. We're not getting any younger here, we have to start thinking about our future, we're not a bunch of horny teenagers anymore…" Elena gave him a pointed stare. "Okay maybe I'm some what of a horny teenager, but hey, that's not to say I'm not looking for a possible future wife…"

Elena was surprised to feel her heart sink a little at Damon's words. She couldn't imagine any girl being suitable as Damon's wife nor did she want to think about having to share Damon's unconditional love and attention.

"And after you being burned by that asshole of an ex and me getting fucked over by Andie, we have the right to be picky." Elena saw red at the mention of Andie's name. Back in college, Damon dated Andie for two years before discovering that she was only using Damon for his money and professional connections from his family's business. Elena always had a hunch that she was bad news and couldn't stand to hear her name even years later after leaving her best friend completely heart broken.

"I mean it might take time for us to find that perfect someone, but until then, we can enjoy each other." Damon wiggled his eyebrows and rolled on top of Elena. They both giggled and slowly brought their lips together. The kiss quickly turned heated as their tongues explored the familiar territory of each other. Elena's hands roamed the wide expanse of Damon's muscular back while his hands traveled from her slim waist up to the bottom of her tank top. While pushing up the material he splayed his large hands against her flat stomach, loving the contrasting feeling of her silky smooth skin against his rough large hands. Elena could kiss Damon all day long if she could. He was hands down the best kisser she has ever encountered. He knew exactly how to put enough passion and softness in the kiss to bring her weak to the knees. She was easily ready for him to just slide right into her after a couple minutes of kissing. But before things went any farther, a soft knock was heard from the door.

"Elena?" Caroline's soft voice echoed from outside the doorway.

Damon groaned and rolled to the side of Elena's body and pushed his face into the pillow to wallow in disappointment. Elena pushed herself to the edge of her bed and straightened out her tank top and ran her hand through her hair, in hope to tame the unruly hair. She walked herself to the door and opened it to find a nervous Caroline.

"Hey, can I talk to you?" The young blonde asked apprehensively.

"Yeah, uh come in."

Damon got up from his place on the bed and walked passed Caroline with a death glare. "Impeccable timing Caroline."

Caroline quickly caught on to the sight before her. Damon and Elena's messy hair and wrinkled clothing all but meant she interrupted them getting hot and heavy…oops. Maybe calling ahead would have been a better idea than just a surprise attack.

"Well since you two need to talk, I'll be going…"Damon spoke while nonchalantly adjusting his uncomfortable hard on in his pants. "Be nice, no bloodshed." He winked before placing a gently kiss upon Elena's forehead. "I'll call you later."

Damon gave a silent warning to Caroline and continued to leave the room.

Caroline started the conversation, "Listen, Lena, I never meant to make you upset. Sometimes I just forget about other people's feelings and I just say whatever I'm thinking. I know I'm far from being a perfect best friend, but I'm trying. But you're right, it's your life and you can do whatever your heart desires, regardless of my opinion on it. It's just I hate what that douchelord did to you. When he hurt you, he hurt me too. But I guess I just want to prove to you that all guys aren't like that."

"I know Care and I appreciate you looking out for me, that's why you're my best friend and why I love you. But you just have to understand that I need to make my own choices and mistakes so that I can learn from them. I'll start to date again…it just might not be as soon as you want me to, but I'll get there."

Caroline nodded in understanding and leaned forward to bring her best friend into a warm embrace. "So am I forgiven?" The blonde asked.

"Of course Care! I'm sorry for just leaving you like that at lunch, I just didn't want to make things any worse."

"Don't worry Lena, I understand completely. I would've done the same thing. I love you Elena and I'm so happy I have you as my best friend."

"I love you to Caroline and I'm just as lucky." She smiled.

Elena's phone went off beside them and the brunette reached over to see the caller i.d.. Seeing that her manager from the bar was calling, she immediately answered.

"Hey Mike, what's up?"

"Hi Elena, I hate to do this to you on your day off but Lisa and I have the first ultrasound for the baby today and I thought I would have enough time to train the new bartender before the appointment but the girl is running late. So would you do me a huge favor and come by and start training her?"

"Of course Mike, you don't have to ask me twice! I'll leave my place now and get there as soon as I can. Goodluck with the ultrasound, can't wait to see the pictures next time I see you!"

"Thank you so much Elena, I owe you!"

"No problem! Talk to you later."

* * *

After saying a quick goodbye to Caroline, Elena made her way to the bar. Even though she didn't know the new girl she was about to train, she was optimistic about having a new friend at work. Having to work with a male majority staff, she was glad another female was joining her.

Walking into the bar she quickly spotted a girl standing next to Mike and assumed that she was the girl she was going to train. She looked to be a young girl around 5'6, long dark chocolate brown hair (a lot similar to her own), wearing tightest and smallest skirt Elena has ever seen.

Mike spotted Elena walking in, "Hey Elena, you're just in time. This is Katherine Pierce. Katherine, this is Elena, she will be training you today. Oh and she is easily the best bartender here, so listen carefully." Mike spoke while winking after the latter statement.

Elena extended her hand and gave Katherine a warm smile, "Hi, it's nice to meet you."

Katherine's judgy eye's looked Elena up and down before returning a barely there smile, all while ignoring Elena's outstretched hand. "Yeah, it is."

Elena pulled her hand back and quickly realized Katherine would not become one of her friend's…unlike she previously thought. _Oh, isn't this going to be fun…_ She thought sarcastically.

**A/N: Oh boy, here's where the fun begins. I just want to make it clear that Katherine doesn't know Elena is Damon's best friend nor does Elena know Damon went out on a 'date' with Katherine…just yet. I hope you enjoyed this chapter. Thank you again for the reviews on last chapter. I get extremely motivated by all of your words. So that being said…the more reviews, the faster I get each chapter out. Thanks again for the R&R!**


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